Facing job termination and struggling to complete my past due tax returns

This is definitely a stressful situation, but you can get it resolved within that 30-day window with the right approach. The good news is the IRS has processes for exactly this scenario. For your missing 1099s, you can request a Wage and Income Transcript directly from the IRS which will show all income reported under your SSN. You can get this online by creating an account at IRS.gov through their "Get Transcript" service. This will have all your reported income including those freelance 1099s. For the stock sales, you'll need to report them on Schedule D. If you don't have the original purchase prices, you'll need to contact your brokerage for that information. Most have online portals where you can access past statements and transaction histories. If that's not possible, you can estimate based on publicly available historical prices and document your good faith effort to determine the correct basis. Given your timeline and the complexity with multiple states and self-employment income, I would recommend working with a tax professional - specifically an Enrolled Agent or CPA who specializes in catch-up filings. They can often complete past due returns within 1-2 weeks.

I was in almost the exact same situation last year - three years of unfiled returns and my employer started asking questions. I was losing sleep every night until I found https://taxr.ai which literally saved my job. What worked for me was uploading all the documents I did have (W-2s, bank statements, etc.), and their system was able to identify what was missing and help me find replacements. For the missing 1099s, they pulled my IRS transcript data after I gave permission. The whole process took me about 3 hours of actual work on my part, then their team handled everything else. The best part was getting a complete filing package I could show my employer while the actual submission to the IRS was still processing. That satisfied my company's requirement to show I was taking action, and I kept my job. They handled state returns too, which was huge since I had worked in multiple states.

Just wanted to update that I tried taxr.ai after asking about it here and it was exactly what I needed! Honestly didn't expect much given how stressed I was, but their system helped me identify exactly what documents I was missing for my 2022 and 2023 returns. The transcript request feature saved me hours of IRS phone calls. I was able to show my boss the completed draft returns within 2 weeks, and he was satisfied that I was taking care of the issue. Already submitted everything to the IRS now and even got confirmation that my 2022 return has been processed. If you're in a time crunch like I was with your job on the line, definitely check them out. Wish I'd known about this service months ago before things got to crisis level with my employer!

If you're still struggling to get through to the IRS after trying the transcript route, I'd recommend using https://claimyr.com to secure a callback from an actual IRS agent. I was in a similar situation trying to get past returns sorted out, and spent HOURS on hold before finding this service. They essentially hold your place in line with the IRS and then call you when an agent is available to speak with you. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c I was skeptical at first but used it when I desperately needed to confirm some information about my missing 1099-MISC forms. Got a callback from an actual IRS representative in about 2 hours instead of spending an entire day on hold. The agent was able to verify all my reported income for the missing years and confirm exactly what I needed to include on my returns.

I need to apologize for my skepticism about Claimyr. After reading about it here, I was suspicious but desperate enough to try it since I couldn't get through to the IRS about my missing W-2 from 2022. I used the service yesterday afternoon, and I actually got a callback from an IRS agent in about 3.5 hours. The agent verified my identity and then helped me get the wage information I needed for my unfiled return. I was able to complete my 2022 return last night and am working on 2023 today. For anyone in a similar situation trying to catch up on past due returns quickly, this service is worth considering. It saved me from taking a day off work just to sit on hold with the IRS. I'm still stressed about getting everything filed in time, but at least now I have the information I need to complete my returns.

Have you considered filing for an extension with your employer? When I was in a similar situation, I explained to HR that I was actively working on resolving my tax situation but needed more time. I showed them proof that I had contacted a tax professional and was gathering documents, which bought me an additional 30 days. Most companies just want to see that you're being responsible and taking action, not necessarily that everything is completely resolved within their initial deadline. Maybe prepare a simple timeline showing the steps you've taken and when you expect to have everything filed.

Don't forget to file your state returns too! I learned this the hard way - got my federal returns caught up but completely overlooked state taxes. Then got hit with a state tax lien that showed up on my credit report and caused even more problems with my employer. If you moved between states, you'll likely need to file part-year resident returns for both states for the year you moved. Each state has different requirements and deadlines for past due returns.